NO315493B1 - Novel sweetening compositions of immediate solubility containing oheperperine dihydrocalcone and at least one other high-intensity sweetening agent, and use thereof - Google Patents
Novel sweetening compositions of immediate solubility containing oheperperine dihydrocalcone and at least one other high-intensity sweetening agent, and use thereof Download PDFInfo
- Publication number
- NO315493B1 NO315493B1 NO19983552A NO983552A NO315493B1 NO 315493 B1 NO315493 B1 NO 315493B1 NO 19983552 A NO19983552 A NO 19983552A NO 983552 A NO983552 A NO 983552A NO 315493 B1 NO315493 B1 NO 315493B1
- Authority
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- Norway
- Prior art keywords
- dihydrochalcone
- neohesperidin
- weight
- sweetener
- sweeteners
- Prior art date
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- 235000003599 food sweetener Nutrition 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 239000003765 sweetening agent Substances 0.000 title claims abstract description 32
- 239000001329 FEMA 3811 Substances 0.000 claims abstract description 47
- ITVGXXMINPYUHD-CUVHLRMHSA-N neohesperidin dihydrochalcone Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ITVGXXMINPYUHD-CUVHLRMHSA-N 0.000 claims abstract description 47
- 229940089953 neohesperidin dihydrochalcone Drugs 0.000 claims abstract description 47
- 235000010434 neohesperidine DC Nutrition 0.000 claims abstract description 47
- 239000008123 high-intensity sweetener Substances 0.000 claims abstract description 15
- 235000013615 non-nutritive sweetener Nutrition 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000004615 ingredient Substances 0.000 claims description 13
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 235000019204 saccharin Nutrition 0.000 claims description 6
- 229940081974 saccharin Drugs 0.000 claims description 6
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229940109275 cyclamate Drugs 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 229960005164 acesulfame Drugs 0.000 claims description 4
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims 1
- 238000010348 incorporation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000000047 product Substances 0.000 description 13
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 10
- 238000004090 dissolution Methods 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 6
- 229960001462 sodium cyclamate Drugs 0.000 description 6
- 235000013305 food Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 235000010358 acesulfame potassium Nutrition 0.000 description 3
- 229960004998 acesulfame potassium Drugs 0.000 description 3
- 239000000619 acesulfame-K Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 3
- PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 2
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 229940093503 ethyl maltol Drugs 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 235000015203 fruit juice Nutrition 0.000 description 2
- -1 glycerol Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940043353 maltol Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000004376 Sucralose Substances 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- PARMADWNFXEEFC-UHFFFAOYSA-N bamethan sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[NH2+]CC(O)C1=CC=C(O)C=C1.CCCC[NH2+]CC(O)C1=CC=C(O)C=C1 PARMADWNFXEEFC-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 235000020094 liqueur Nutrition 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/36—Terpene glycosides
Abstract
Description
Foreliggende oppfinnelse angår nye søtningsmiddelsammensetninger med umiddelbar oppløselighet forsterket av neohesperidin-dihydrocalkon og minst ett annet høyintensi-" tetssøtninsstoff såvel som deres anvendelse som søtningsmidler. The present invention relates to new sweetener compositions with immediate solubility enhanced by neohesperidin dihydrochalcone and at least one other high-intensity sweetener as well as their use as sweeteners.
Som høyintensitetssømingsmidler innen rammen av foreliggende oppfinnelse, kan nevnes sakkarin, cyklamat, acesulfam og deres akseptable salter, for anvendelse for mennesker og dyr. De nye sammensetningene kan bli benyttet som søtningsstoff for en hvilken som helst type mat, drikke, farmasøytika, veterinæriske og kosmetiske preparater samt fbr. Oppløseligheten og oppløselighetsraten til de nye sammensetningene gitt ved foreliggende oppfinnelse, er signifikant høyere enn de til neohesperidin-dihydrocalkon alene, i en slik grad at de kan bli klassifisert som umiddelbart oppløselige sammensetninger. As high-intensity suture agents within the scope of the present invention, saccharin, cyclamate, acesulfame and their acceptable salts, for use in humans and animals, can be mentioned. The new compositions can be used as sweeteners for any type of food, drink, pharmaceutical, veterinary and cosmetic preparations as well as e.g. The solubility and dissolution rate of the new compositions provided by the present invention are significantly higher than those of neohesperidin-dihydrochalcone alone, to such an extent that they can be classified as immediately soluble compositions.
Neohesperidin-dihydrocalkon er et høyintensistessøtningsmiddel og en smaksmodulator som kan bli fremstilt fra visse flavonoider funnet i sitrusfrukter (Bar A. et al., Lebens-mittel Wissenchaft und Technologi (1990) 23,371-376; Horowitz R. M. og Gentili B., i Alternative Sweetners (1991), 2. utgave, Nabors L.O. og Gelardi R.C. (Eds.), s. 97-116, Marcel Dekker ing., N.Y.). Fremstillingen av neohesperidin-dihydrocalkon har blitt beskrevet i forskjellige patenter, US 3087821, US 3375242, JP 48/57960, GB 1443310, JP 50/149635, JP 50/154261 og ES 545276. Neohesperidin dihydrochalcone is a high intensity sweetener and flavor modulator that can be produced from certain flavonoids found in citrus fruits (Bar A. et al., Lebens-mittel Wissenchaft und Technologi (1990) 23,371-376; Horowitz R. M. and Gentili B., in Alternative Sweetners (1991), 2nd ed., Nabors L.O. and Gelardi R.C. (Eds.), pp. 97-116, Marcel Dekker Eng., N.Y.). The preparation of neohesperidin dihydrochalcone has been described in various patents, US 3087821, US 3375242, JP 48/57960, GB 1443310, JP 50/149635, JP 50/154261 and ES 545276.
Anvendelsen av neohesperidin-dihydrocalkon som et søtningsmiddel i mat, har blitt beskrevet i US-patent nr. 4087588 og av Montijano H. og Borrego, F. i: LFRA Ingredients Handbook (Sweeteners), 1996, Dalzell J. (Eds.), Leatherhead Food Research Assosciation, s. 181-200. The use of neohesperidin dihydrochalcone as a sweetener in food has been described in US Patent No. 4087588 and by Montijano H. and Borrego, F. in: LFRA Ingredients Handbook (Sweeteners), 1996, Dalzell J. (Eds.), Leatherhead Food Research Association, pp. 181-200.
For tiden er det vanlig praksis å anvende søtningsstoffkombinasjoner for å forbedre søt-ningsprofilen og redusere oppfattelsen av bitter smak eller andre uønskede fenomener. Disse søtningsmiddelkombinasjonene kan vanligvis bli preparert ved enkel blanding av individuelle ingredienser. Hovedulempen ved disse således produserte søtningsmiddel-kombinasjonene er en mulig disaggregering av deres individuelle ingredienser. Syner-gi sme er også en vanlig egenskap ved binære søtningsmiddelkombinasjoner. Således har neohesperidin-dihydrocalkon blitt rapportert å vise viktige synergistiske effekter i kombinasjon med sakkarin (US-patent nr. 3653923) og sukralose (EP 507598), såvel som med andre høyintensitetssøtningsstoffer, sukkere og polyoler (Schiffman S.S. et al., Currently, it is common practice to use sweetener combinations to improve the sweetening profile and reduce the perception of bitter taste or other undesirable phenomena. These sweetener combinations can usually be prepared by simple mixing of individual ingredients. The main disadvantage of these sweetener combinations thus produced is a possible disaggregation of their individual ingredients. Synergism is also a common property of binary sweetener combinations. Thus, neohesperidin dihydrochalcone has been reported to exhibit important synergistic effects in combination with saccharin (US Patent No. 3653923) and sucralose (EP 507598), as well as with other high-intensity sweeteners, sugars and polyols (Schiffman S.S. et al.,
Brain Research Bulletin (1995) 38, s. 105-220). Brain Research Bulletin (1995) 38, pp. 105-220).
Anvendelsen av neohesperidin-dihydrocalkon ved lave konsentrasjoner som en smaks-modifikator, har blitt beskrevet i EP 500977 og US-patent nr. 5300309.1 tillegg angår * WO-patent 96/17527 kombinasjoner av neohesperidin-dihydrocalkon med (a) maltol, (b) etylmaltol og (c) maltol og etylmaltol for å modifisere smaken av neohespeirdin-dihydrocalkon. The use of neohesperidin dihydrochalcone at low concentrations as a flavor modifier has been described in EP 500977 and US patent no. 5300309.1 additionally concerns * WO patent 96/17527 combinations of neohesperidin dihydrochalcone with (a) maltol, (b) ethyl maltol and (c) maltol and ethyl maltol to modify the taste of neohespeirdin dihydrochalcone.
Ett av de essensielle kravene som må bli tatt hensyn til ved valg av et høyintensivt søtningsmiddel, er at dets oppløselighet i vann blir øket ved omgivelsestemperatur. Oppløseligheten til neohesperidin-dihydrocalkon er lav, 0,4-0,5 g/l, og dets oppløse-lighetsrate er også lav (Montijano H. og Borrego, F. I: LFRA Ingredients Handbook (Sweeteners), 1996, Dalzell J. (Eds.), Leatherhead Food Research Association, s. 181-200. Denne lave oppløseligheten og oppløselighetsraten til neohesperidin-dihydrocalkon begrenser deres anvendelse, da de hindrer visse fremgangsmåter for fremstilling av produkter som er gjort søte med neohesperidin-dihydrocalkon, og gjør det umulig å prepa-rere siruper og konsentrater med et slikt søtningsmiddel. For dette formål har monoba-siske salter av neohesperidin-dihydrocalkon med høyere oppløselighet enn det opprinne-lige dihydrocalkon, blitt beskrevet (US-patenter nr. 3984394 og 4031260). Imidlertid viser disse saltene en høyere grad av ustabilitet, selv i fast form, på grun av deres sterkt alkaliske natur, noe som gjør anvendeligheten til disse saltene meget begrenset. One of the essential requirements that must be taken into account when choosing a high-intensity sweetener is that its solubility in water is increased at ambient temperature. The solubility of neohesperidin dihydrochalcone is low, 0.4-0.5 g/l, and its dissolution rate is also low (Montijano H. and Borrego, F. I: LFRA Ingredients Handbook (Sweeteners), 1996, Dalzell J. (Eds.), Leatherhead Food Research Association, pp. 181-200.This low solubility and dissolution rate of neohesperidin dihydrochalcone limits their use, as they hinder certain methods of making products sweetened with neohesperidin dihydrochalcone, and make impossible to prepare syrups and concentrates with such a sweetener. For this purpose monobasic salts of neohesperidin dihydrochalcone with higher solubility than the original dihydrochalcone have been described (US Patents Nos. 3984394 and 4031260). However, these salts have a higher degree of instability, even in solid form, due to their strongly alkaline nature, which makes the applicability of these salts very limited.
US-patent nr. 4254155 og US-patent nr. 4304794 beskriver oppløselige kombinasjoner av neohesperidin-dihydrocalkon med polyhydroksylerte forbindelser slike som glyserol, sukker, arabisk gummi, carrageenan, karboksylmetylcellulosepektin osv., med sensoris-ke egenskaper som også er optimalisert med hensyn til utgangsforbindelsen. Hovedulempen ved disse kombinasjonene, er at de inneholder stoffer hvis funksjon er frem-mede for selve prosessen for søtning av slike produkter som mat, for, farmasøytika og veterinærpreparater. US Patent No. 4,254,155 and US Patent No. 4,304,794 describe soluble combinations of neohesperidin dihydrochalcone with polyhydroxylated compounds such as glycerol, sugar, gum arabic, carrageenan, carboxymethyl cellulose pectin, etc., with sensory properties that are also optimized with respect to the output connection. The main disadvantage of these combinations is that they contain substances whose function is foreign to the actual process of sweetening such products as food, fodder, pharmaceuticals and veterinary preparations.
Følgelig er tilgjengelige forbedrede kombinasjoner av neohesperidin-dihydrocalkon som øker dets oppløselighet i vann ved omgivelsestemperatur, nødvendige. Accordingly, available improved combinations of neohesperidin-dihydrochalcone that increase its solubility in water at ambient temperature are needed.
Det er nå overraskende funnet av visse kombinasjoner av neohesperidin-dihdyrocalkon med andre høyintensitetssøtningsmidler kan bli fremstilt på en slik måte at oppløselig-hetsegenskapene til neohesperidin-dihydrocalkon i sluttproduktet er signifikant forbed-ret i forhold til det rene produktet. It has now surprisingly been found that certain combinations of neohesperidin-dihydrochalcone with other high-intensity sweeteners can be produced in such a way that the solubility properties of neohesperidin-dihydrochalcone in the final product are significantly improved compared to the pure product.
Således angår foreliggende oppfinnelse nye søtningsmiddelsammensetninger med umiddelbar oppløselighet i vann, inneholdende neohesperidin-dihydrocalkon og minst et annet høyintentistetssøtningsmiddel, hvori vektforholdet mellom neohesperidin-dihydrocalkon og de andre søtningsmidlene er mellom 1:999 og 1:4,5, kjennetegnet ved at den oppnås ved en fremgangsmåte som innbefatter inkorporering enten av en løsning av 1 vektdel neohesperidin-dihydrocalkon i en vandig løsning som inneholder fra 4,5 til 999 vektdeler annet søtningsmiddel, eller en løsning av 1 vektdel neohesperidin-dihydrocalkon i et egnet løsemiddel forskjellig fra vann og deretter tilsette 4,5 til 999 vektdeler av et annet søtningsstoff og til slutt tørking. Thus, the present invention concerns new sweetener compositions with immediate solubility in water, containing neohesperidin-dihydrochalcone and at least one other high-intensity sweetener, in which the weight ratio between neohesperidin-dihydrochalcone and the other sweeteners is between 1:999 and 1:4.5, characterized in that it is obtained by a method comprising incorporating either a solution of 1 part by weight of neohesperidin dihydrochalcone in an aqueous solution containing from 4.5 to 999 parts by weight of other sweetener, or a solution of 1 part by weight of neohesperidin dihydrochalcone in a suitable solvent other than water and then adding 4.5 to 999 parts by weight of another sweetener and finally drying.
I samsvar med foreliggende oppfinnelse kan den lave oppløseligheten og oppløselighets-raten til neohesperidin-dihydrocalkon i vann bli betydelig kompensert ved anvendelsen av sammensetningene ifølge foreliggende oppfinnelse. På denne måten kan opplø-seligheten til neohesperidin-dihydrocalkon i vann bli øket inntil omkring 165 ganger, avhengig av den spesifikke kombinasjonen. Dette muliggjør dets håndtering i industriel- In accordance with the present invention, the low solubility and solubility rate of neohesperidin dihydrochalcone in water can be significantly compensated by the use of the compositions according to the present invention. In this way, the solubility of neohesperidin dihydrochalcone in water can be increased up to about 165 times, depending on the specific combination. This enables its handling in industrial
le prosesser. le processes.
Foreliggende søknad beskriver også en fremgangsmåte for fremstilling av slike søt-ningsmiddelsammensetninger ved hjelp av oppløsningen av en neohesperidin-dihydrocalkon (a) i en konsentrert vandig oppløsning av andre høyintensitetssøtningsmidler (b), og påfølgende samtørking av sammensetningen for å danne et homogent pulver som er mer oppløselig i vann enn de individuelle ingrediensene. The present application also describes a method for producing such sweetener compositions using the solution of a neohesperidin dihydrochalcone (a) in a concentrated aqueous solution of other high-intensity sweeteners (b), and subsequent co-drying of the composition to form a homogeneous powder which is more soluble in water than the individual ingredients.
Høyintensitetssøtningsmidlet kan inneholde, på en ikke-begrensende måte, for eksempel sakkarin, cyklamat, acesulfam og deres akseptable salter for konsumpsjon av mennesker og dyr. Uttrykkene sakkarin og cyklamat benyttet i foreliggende oppfinnelse, er spesifikt referert til sakkarin og cyklamat enten i syreform eller i form av deres ammonium, alkalisalter slik som natrium- eller kaliumsalt, eller jordalkalimetallsalter slik som kal-sium- eller magnesiumsalter. Det samme gjelder for acesulfam. Dets kaliumsalt er foretrukket. The high intensity sweetener may contain, in a non-limiting manner, for example, saccharin, cyclamate, acesulfame and their acceptable salts for human and animal consumption. The terms saccharin and cyclamate used in the present invention refer specifically to saccharin and cyclamate either in acid form or in the form of their ammonium, alkali salts such as sodium or potassium salts, or alkaline earth metal salts such as calcium or magnesium salts. The same applies to acesulfame. Its potassium salt is preferred.
Fremgangsmåten for fremstilling kan bli modifisert ved anvendelse av andre passende oppløsningsmidler, slik som for eksempel alkoholer, og selv ved å holde ingrediensen (b) i sammensetningen i suspensjon i en oppløsning av (a). Likeledes kan det vandige medium, i hvilket ingrediensene (a) og (b) blir funnet oppløst, bli benyttet direkte, for eksempel i en fremgangsmåte som leder til en nær assosiering av ingrediensene, slik som sprøytetørkingsprosessen. En ekspert innen området vil lett kunne bestemme betingelsene med hvilke en sprøytetørkingsprosess kan bli utført. The method of preparation can be modified by using other suitable solvents, such as, for example, alcohols, and even by keeping the ingredient (b) of the composition in suspension in a solution of (a). Likewise, the aqueous medium in which the ingredients (a) and (b) are found dissolved can be used directly, for example in a method which leads to a close association of the ingredients, such as the spray drying process. An expert in the field will easily be able to determine the conditions under which a spray drying process can be carried out.
Ingrediensene (a) og (b) i søtningssammensetningen ifølge foreliggende oppfinnelse, The ingredients (a) and (b) in the sweetening composition according to the present invention,
kan bli kombinert ved et hvilket som helst vektforhold. Imidlertid er det foretrukne vekt-forhold av neohespendin-dihydrocalkonsøtningsmiddel til andre høyintensitets-søtningsmidler i området 1:999 til 1:4,5, mest foretrukket mellom 1:99 og 1:7. can be combined at any weight ratio. However, the preferred weight ratio of neohespendin dihydrochalcone sweetener to other high intensity sweeteners is in the range of 1:999 to 1:4.5, most preferably between 1:99 and 1:7.
Det er nå funnet at oppløseligheten og oppløselighetsraten til neohesperidin-dihydrocalkon i slike søtningsmiddelsammensetninger økes i sterk grad. Oppløseligheten til neohesperidin-dihydrocalkon er derfor høyere enn den forventet fra dets egen oppløselighet eller fra dets prepareringer oppnådd ved en enkel blanding av dens ingredienser. Denne effekten er overraskende og spesifikk, noe som ikke blir observert i sammenheng med fremgangsmåten beskrevet fra andre søtningsmidler. It has now been found that the solubility and dissolution rate of neohesperidin dihydrochalcone in such sweetener compositions is greatly increased. The solubility of neohesperidin dihydrochalcone is therefore higher than that expected from its own solubility or from its preparations obtained by simple mixing of its ingredients. This effect is surprising and specific, which is not observed in the context of the method described from other sweeteners.
Søtningsmiddelsammensentingen fremstilt ifølge den beskrevne fremgangsmåten har ytterligere fordeler sammenlignet med blandinger av de individuelle ingrediensene ved at de ikke disintegrerer i sine ingredienser. The sweetener composition prepared according to the described method has further advantages compared to mixtures of the individual ingredients in that they do not disintegrate into their ingredients.
Foreliggende oppfinnelse angår også anvendelse av sammensetningen som definert i medfølgende krav 1 til 5 for å søtgjøre produkter hvori høyintensitetssøtningsmidler pr. The present invention also relates to the use of the composition as defined in accompanying claims 1 to 5 to sweeten products in which high-intensity sweeteners per
i dag anvendes. today is used.
Søtningsmiddelsammensetningene gitt ved foreliggende oppfinnelse, kan bli benyttet for søtning av mange forskjellige produkter. De kan også bli benyttet for søtning av et hvilket som helst produkt hvor høyintensitetssøtningsmidler blir benyttet, eller for fremstilling av bordsøtningsmidler. Eksempler på slike produkter er faste og flytende matvarer og drikker, slik som melkeprodukter (yoghurt, puddinger, vaniljekrem), kaffe, The sweetener compositions provided by the present invention can be used to sweeten many different products. They can also be used for sweetening any product where high intensity sweeteners are used, or for the production of table sweeteners. Examples of such products are solid and liquid foods and drinks, such as milk products (yoghurt, puddings, vanilla cream), coffee,
te, kakao, pulverdrikker, brusende drikker, fruktjuicer, fruktjuicedrikker, alkoholiske drikker (aperitiffer, bittere, likører), bakevarer (kjekser, kaker), godterier (slikkerier, geléer, sjokolader), tyggegummier o.l. Eksempler på andre produkter som kan benytte søtningsmidler ifølge foreliggende oppfinnelse, er de for dyrefor (for o.l.), farmasøytiske og veterinære preparater og kosmetiske preparater (orale hygienemidler o.l.). tea, cocoa, powdered drinks, fizzy drinks, fruit juices, fruit juice drinks, alcoholic drinks (aperitifs, bitters, liqueurs), baked goods (biscuits, cakes), candies (candies, jellies, chocolates), chewing gums etc. Examples of other products that can use sweeteners according to the present invention are those for animal feed (for etc.), pharmaceutical and veterinary preparations and cosmetic preparations (oral hygiene products etc.).
Søtningsmiddelsammensetningene gitt ved foreliggende oppfinnelse, kan bli benyttet for The sweetener compositions provided by the present invention can be used for
å søtgjøre produkter per se, for eksempel ved sammenblanding med produktet som skal søtgjøres i forskjellige fysiske former, slik som pulvere, tabletter, belagte tabletter, kom to sweeten products per se, for example by mixing with the product to be sweetened in different physical forms, such as powders, tablets, coated tablets, etc.
osv., og i kombinasjon med bærere (stivelse, dekstriner og andre modifiserte stivelser, sorbitol, xylitol, maltitol, glukose, fruktose, sitronsyre, vanlig salt, kalsiumfosfat osv.)' og adjuvanter (bikarbonater, karbohydrater osv.) eller andre ikke-toksiske stoffer som er forenelige med produktet som skal søtgjøres. etc., and in combination with carriers (starch, dextrins and other modified starches, sorbitol, xylitol, maltitol, glucose, fructose, citric acid, common salt, calcium phosphate, etc.)' and adjuvants (bicarbonates, carbohydrates, etc.) or other non- toxic substances compatible with the product to be sweetened.
Foreliggende oppfinnelse vil bli illustrert ved de følgende eksempler. The present invention will be illustrated by the following examples.
Eksempel 1: Sammensetning av neohesperidin-dihydrocalkon: kaliumacesulfam (7:93) 93 g kaliumacesulfam blir oppløst i 107 ml vann under forsiktig omrøring og oppvarming (50°C). Straks det ble oppnådd en klar oppløsning, ble 7 g neohesperidin-dihydrocalkon tilsatt og omrørt inntil fullstendig oppløsning, og så ble vannet fjernet under vakuum. Et hvitaktig faststoff ble oppnådd tilsvarende sammensetningen av neohesperidin-dihydrocalkon:kaliumacesulfam (7:93) med en oppløselighet i vann ved romtemperatur over 140 g/l (ekvivalent oppløselighet til neohesperidin-dihydrocalkon var høyere enn 10 g/liter). Example 1: Composition of neohesperidin dihydrochalcone: acesulfame potassium (7:93) 93 g of acesulfame potassium are dissolved in 107 ml of water with gentle stirring and heating (50°C). As soon as a clear solution was obtained, 7 g of neohesperidin dihydrochalcone was added and stirred until complete dissolution, and then the water was removed under vacuum. A whitish solid was obtained corresponding to the composition of neohesperidin-dihydrochalcone:acesulfame potassium (7:93) with a solubility in water at room temperature above 140 g/l (equivalent solubility of neohesperidin-dihydrochalcone was higher than 10 g/liter).
Eksempel 2: Sammenetning av neohesperidin-dihydrocalkonmatriumcyklamat (10:90) Example 2: Composition of neohesperidin-dihydrochalcone sodium cyclamate (10:90)
I en 1 liters flatbunnet, rund flaske ble 20 g neohesperidin-dihydrocalkon veid og bragt In a 1-liter flat-bottomed, round bottle, 20 g of neohesperidin-dihydrochalcone was weighed and brought
til et volum med 400 g metanol under omrøring inntil fullstendig oppløsning. 180 g vannfri natriumcyklamat ble tilsatt og omrørt i 30 minutter. Natriumcyklamatet forble i suspensjon i metanoloppløsningen av neohesperidin-dihydrocalkon. Oppløsningsmidlet ble avdampet ved 40-45°C. Det oppnådde faststoffet tilsvarer sammensentingen av neohesperidin-dihydrocalkon:natriumcyklarnat (10:90) med en oppløselighet i vann ved romtemperatur på opptil 200 g/l, noe som er indikativt for en ekvivalent oppløselighet av neohesperidin-dihydrocalkon ekvivalent opptil 20 g/l. to a volume of 400 g of methanol with stirring until complete dissolution. 180 g of anhydrous sodium cyclamate was added and stirred for 30 minutes. The sodium cyclamate remained in suspension in the methanol solution of neohesperidin dihydrochalcone. The solvent was evaporated at 40-45°C. The solid obtained corresponds to the composition of neohesperidin dihydrochalcone:sodium cyclate (10:90) with a solubility in water at room temperature of up to 200 g/l, which is indicative of an equivalent solubility of neohesperidin dihydrochalcone equivalent up to 20 g/l.
Eksempel 3: Sammensetning av neohesperidin-dihydrocalkon:natriumsakkarin (12:88) Example 3: Composition of neohesperidin-dihydrochalcone:sodium saccharin (12:88)
88 g natriumsakkarin ble veid og oppløst i 150 g vann under omrøring ved romtemperatur. Så ble 12 g neohesperidin-dihydrocalkon tilsatt og omrørt inntil fullstendig oppløs-ning. Straks oppløsningsmidlet ble fjernet under vakuum, ble et hvitaktig pulver oppnådd, tilsvarende sammensetningen av neohe$peridin-dihydrocalkon:natriurnsakkarin (12:88), med en oppløselighet i vann ved romtemperatur over 500 g/l (ekvivalent opp-løselighet av neohesperidin-dihydrocalkon var høyere enn 60 g/liter). 88 g of sodium saccharin were weighed and dissolved in 150 g of water with stirring at room temperature. Then 12 g of neohesperidin dihydrochalcone were added and stirred until complete dissolution. Immediately the solvent was removed under vacuum, a whitish powder was obtained, corresponding to the composition of neohe$peridin-dihydrochalcone:sodium urnsaccharin (12:88), with a solubility in water at room temperature above 500 g/l (equivalent solubility of neohesperidin-dihydrochalcone was higher than 60 g/litre).
Eksempel 4: Sammensetning av neohesperidm-dihydrocalkon:natriumcyklamat:natriumsakkarin (3:79:18) Example 4: Composition of neohesperidm-dihydrochalcone:sodium cyclamate:sodium saccharin (3:79:18)
131,7 g vannfri natriumcyklamat og 30 g natriumsakkarin ble oppløst i 338,3 ml vann 131.7 g of anhydrous sodium cyclamate and 30 g of sodium saccharin were dissolved in 338.3 ml of water
under forsiktig omrøring og oppvarming (50°C). Straks det var oppnådd en klar oppløs-ning, ble 5 g neohesperidin-dihydrocalkon tilsatt og omrørt inntil fullstendig oppløsning, og så ble vannet fjernet under vakuum. Det ble oppnådd et hvitaktig faststoff tilsvarende sammensetningen neohesperidin-dihydrocalkon:natriumcyklamat :natriumsakkarin (3:79:18) med en oppløselighet i vann ved romtemperatur over 430 g/l, fra hvilket den ekvivalente oppløseligheten til neohesperidin-dihydrocalkon var øket 13 ganger. with gentle stirring and heating (50°C). As soon as a clear solution had been obtained, 5 g of neohesperidin dihydrochalcone was added and stirred until complete dissolution, and then the water was removed under vacuum. A whitish solid was obtained corresponding to the composition neohesperidin-dihydrochalcone:sodium cyclamate:sodium saccharin (3:79:18) with a solubility in water at room temperature above 430 g/l, from which the equivalent solubility of neohesperidin-dihydrochalcone was increased 13 times.
Claims (6)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009701939A ES2139518B1 (en) | 1997-09-16 | 1997-09-16 | NEW INSTANT SOLUBILITY SWEETENING COMPOSITIONS IN WATER COMPOSED OF NEOHESPERIDINE DIHIDROCHALCONA WITH ANOTHER OR OTHER HIGH INTENSITY SWEETENERS. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO983552D0 NO983552D0 (en) | 1998-08-03 |
| NO983552L NO983552L (en) | 1999-03-17 |
| NO315493B1 true NO315493B1 (en) | 2003-09-15 |
Family
ID=8300600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19983552A NO315493B1 (en) | 1997-09-16 | 1998-08-03 | Novel sweetening compositions of immediate solubility containing oheperperine dihydrocalcone and at least one other high-intensity sweetening agent, and use thereof |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0908107B1 (en) |
| AT (1) | ATE254408T1 (en) |
| DE (1) | DE69819842T2 (en) |
| DK (1) | DK0908107T3 (en) |
| ES (1) | ES2139518B1 (en) |
| NO (1) | NO315493B1 (en) |
| PT (1) | PT908107E (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201610860UA (en) | 2014-08-05 | 2017-02-27 | Givaudan Sa | Sweetener compositions |
| CN113330018A (en) * | 2018-10-24 | 2021-08-31 | 可口可乐公司 | Dihydrochalcones from Balanophora japonica |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2628294C3 (en) * | 1976-06-24 | 1978-12-14 | Hoechst Ag, 6000 Frankfurt | Sweetener blend with improved sucrose-like taste |
| US3653923A (en) * | 1968-03-20 | 1972-04-04 | Takeda Chemical Industries Ltd | Sweetening composition |
| JPS5716783B2 (en) * | 1974-05-27 | 1982-04-07 | ||
| US5192563A (en) * | 1986-10-22 | 1993-03-09 | Wm. Wrigley, Jr. Company | Strongly mint-flavored chewing gums with reduced bitterness and harshness |
| EP0500977B1 (en) * | 1991-02-26 | 1995-07-05 | Zoster, S.A. | Use of neohesperidin dihydrochalcone for potentiating body and mouthfeel of foods and beverages |
| GB9107142D0 (en) * | 1991-04-05 | 1991-05-22 | Tate & Lyle Plc | Sweetening agents |
-
1997
- 1997-09-16 ES ES009701939A patent/ES2139518B1/en not_active Expired - Fee Related
-
1998
- 1998-08-03 NO NO19983552A patent/NO315493B1/en not_active IP Right Cessation
- 1998-08-31 DE DE69819842T patent/DE69819842T2/en not_active Expired - Lifetime
- 1998-08-31 PT PT98116450T patent/PT908107E/en unknown
- 1998-08-31 EP EP98116450A patent/EP0908107B1/en not_active Expired - Lifetime
- 1998-08-31 DK DK98116450T patent/DK0908107T3/en active
- 1998-08-31 AT AT98116450T patent/ATE254408T1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69819842T2 (en) | 2004-07-29 |
| DK0908107T3 (en) | 2004-03-29 |
| ES2139518B1 (en) | 2000-10-16 |
| DE69819842D1 (en) | 2003-12-24 |
| NO983552D0 (en) | 1998-08-03 |
| EP0908107A2 (en) | 1999-04-14 |
| NO983552L (en) | 1999-03-17 |
| EP0908107B1 (en) | 2003-11-19 |
| ATE254408T1 (en) | 2003-12-15 |
| PT908107E (en) | 2004-04-30 |
| ES2139518A1 (en) | 2000-02-01 |
| EP0908107A3 (en) | 2001-05-23 |
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